In this talk we will explore the evolution of both the Internet's most heavily used transport protocol, TCP, and the current network environment with respect to how this evolving network ultimately impacts end-to-end protocols. The traditional end-to-end assumptions about the Internet as increasingly challenged by the introduction of intermediary network elements (middleboxes) that intentionally or unintentionally prevent or alter the behavior of end-to-end communications. We will show measurement results showing the impact of the current network environment on a number of traditional and proposed protocol mechanisms (e.g., Path MTU Discovery, Explicit Congestion Notification, etc.). In addition, we investigate the prevalence and correctness of implementations using proposed TCP algorithmic and protocol changes (e.g., selective acknowledgment-based loss recovery, congestion window growth based on byte counting, etc.). We present results of measurements taken using an active measurement framework to study web servers and a passive measurement survey of clients accessing information from our web server. We analyze our results in the context of gaining further understanding of the differences between the behavior of the Internet in theory versus the behavior we observed through measurements. In addition, these measurements can be used to guide the definition of more realistic Internet modeling scenarios.